Potassium Carbonate → 1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-4-nitro-1H-pyrazole

Participants

Reaction Steps

To a solution of 4-nitropyrazole (Manchester organics; 0.503 g, 4.45 mmol) in DMF (10 ml) was added potassium carbonate (1.24 g, 9.0 mmol), sodium iodide (24 mg, 0.160 mmol) and then 2-(bromomethyl)-4-chloro-1-[(phenylmethyl)oxy]benzene (synthesised according to WO2006066968; 1.23 g, 3.95 mmol). The reaction was stirred at ambient temperature overnight. A further amount of 2-(bromomethyl)-4-chloro-1-[(phenylmethyl)oxy]benzene (156 mg) was added and the reaction was stirred at ambient temperature for a further 30 min. The reaction mixture was concentrated in vacuo and treated with water (60 ml). The aqueous solution was extracted with ethyl acetate (3×60 ml). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The sample was loaded in dichloromethane and purified on silica (50 g) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound (1.17 g) as a white solid; LCMS (System 1): MH+=344, tRET=3.58 min.

Provenance & Evidence